From bad to worse
by spankingfemfatale
Summary: Takes place at the end of season 1 where Vane tells Jack that he'll never sail under the black again. Of course what could be worse than being stuck at the brothel? Being stuck at the brothel under the former madam Mrs. Mapleton *evil grin* My plot written by my lovely husband! I am loved! :) WARNING! Contains spanking and non-con M/M! Gritty just like the show, you've been warned!


Jack considered himself to be a very witty person. In fact, Jack would once have boasted that there was nothing anyone could say that could shock or surprise him enough to leave him speechless. Many would have agreed with this notion, too; Jack was after all an absolute master in the art of speech.

Nonetheless, here he found himself without words despite his enormous vocabulary and eloquence. He could only blink and stare at Charles as the other man told him that instead of killing him for the alleged act of treason (which he could unfortunately not invalidate without committing very real treason against his partner Anne) he would instead be left to "rot with the whores".

Taking Jack's stunned silence as acceptance of the awful choices left him, Vane smiled, stood, and turned to leave. The former Madam of the house stepped forward, her face positively aglow, "It would seem things have properly asserted themselves", she said, "I told you that you would regret your boyish actions."

Jack ignored her, his mind racing over what all of this meant and grasping the true severity of this rather difficult problem. She continued speaking, perhaps assuming that he cared what she had to say, "I believe even you understand that I will be returning to my previous station as head mistress of this house."

That got Jack's attention; as he looked over to her, she made a grand dismissive gesture, "As I am of course in charge, my first action is going to be to terminate your employment." She hesitated before imitating his previous sarcasm, "Thank you very much."

Jack finally returned to his senses, realizing that he was heading into a death trap, "Madam, we are both aware that if I leave this place that man will kill me. As this is the case, I will still need a means of gainful employment…" Jack paused; he had never been a prideful man, but giving her this still stung, "perhaps we can come to an arrangement?"

She chortled, fanning herself with the little paper fan she always carried with her. The uncomfortable (at least for Jack) silence hung in the air for some few moments before she finally replied in a fashion that made it clear she wished him to suffer a while longer, "I'll think about it. Why don't you… hang around until I make up my mind?"

She laughed at Jack's helpless expression, and finally turned to head upstairs to the small office that Jack had until recently called his own, "I need to get my house in order, now that we are clear on who really runs this place."

Jack let out a lot sigh, realizing he had been holding his breath for a really long time. He glanced up at Anne, who shared his look of worry. Vane had not threatened her specifically, but they both knew without asking that her fate was intertwined with his.

Hell, Charles Vane might even have deduced that the entire betrayal was actually her idea all along, and that she had strong-armed Jack into it. Their antics were, after all, not entirely unknown among their former crew.

Jack took another look at Anne, and saw that she knew what he was thinking as she moved to take a seat at the bar; all that was left now was the waiting.

She made them wait for several days. Anne told Jack that she wished to give the bitch a piece of her mind, but Jack stoically advised her that as Vane technically owned the whore-house, threatening the currently re-instated Madam would prove pointless as they could not back up such hostility.

At last though, Mrs. Mapleton finally deigned to speak to Jack further on the matter, apparently having decided that she had seen him squirm long enough. "You'll be a chore-boy, and Anne will be a bouncer."

Jack licked his lips, knowing that his inferior title was most likely non-negotiable (because it was obviously another in a long list of punishments bound to come) but figuring it wouldn't hurt to try, "You know, I have spent some amount of time under the black flag; I assure you that I could likewise make a fearsome guardian for this fine establishment."

Mrs. Mapleton smiled and patted his cheek, "Oh you couldn't scare a fly, my dear. No, I think you are far better served in a more… menial position."

Jack nodded, having entirely expected this reaction, but finding himself with little choice in the matter. At least she hadn't tried to have Anne become a whore; that would almost certainly have ended in disaster. "Very well… Madam, it will be as you say."

The mistress of the house only smiled at his obviously begrudging tone, and waved her hand at him, "You shall begin work at once; see to it that those table over there are bussed and that my girls don't need anything."

Jack nodded and moved to tell Anne about the new development on his way to the indicated tables, when Mrs. Mapleton called out to him once more, her voice filled with wry amusement, "Oh, and Jack… I'll be checking in on you occasionally; I don't think I need to remind you how much incentive you have to be diligent in your duties…"

Jack only nodded again, deciding then that he now thoroughly hated this woman. Jack wasn't prone to hate; usually stupid people or people who tried to push him around only annoyed him, but no, no this woman he hated with all of his heart.

She would be ousted again, of that he promised himself. It would just take time and a plan, so he would play along with her insulting schemes for the time being, and grant himself the reprieve needed to think.

So it was that Jack Rackham, former quartermaster under the profitable Charles Vane was now a lowly servant to a whore-house Madam, cleaning tables, serving drinks to drunken sailors and scrubbing vomit off the baseboards.

This went on for several days and though Jack tried hard to find a way out of the particular mess he was in, he found himself rebuffed at all corners. Max had been demoted back to whore (the only reason Mrs. Mapleton had not thrown her into the streets being her fear of Mrs. Guthrie) and despite Jack's insistent pleas to repay his kindness by seeking aid from Mrs. Guthrie she repeatedly turned him down. Apparently she would rather die than ask for help from Eleanor.

Anne was less than helpful, becoming entirely too comfortable in her new position as hired thug for the house, especially since Mrs. Mapleton actually paid her well. Jack was surprised at first but quickly realized that the old crone was only separating him further from his allies.

He realized the strategy was working when after he consulted Anne on how they might remedy the new situation she told him, "Give it up, Jack; she has you by the balls… besides, I think your new position rather suits you. Maybe if you do well enough she'll promote you to advisor or something, since you aren't good at much else."

Jack did his best to hide his offense, knowing that Anne only got off on it, and tried his luck with a variety of other deckhands whom he knew little or nothing about. They all laughed him away, though. Tale of how he had 'betrayed' his crew had spread like the plague, just as Vane had promised it would, and he couldn't even get anyone to hear him through an entire sentence.

This only left him with the least capable to fall back on, which he didn't bother with; after all, if he put his faith in the dumbest swindlers in Nassau, he's just end up dead for his efforts. Occasionally as he made these rounds he would catch the Madam watching him, and from the small smile she always wore, he could tell that not only did she know what he was 'secretly' doing, she thought it amusing.

Just keep smiling you old whore; thought Jack, no one holds all the cards all the time, and one day you'll see who you're messing with.

Weeks passed him by and Jack's frustration grew as he watched the Madam take measures to circumvent his departure from his current circumstances. Even should he become desperate enough to try to flee the island entirely, she had, according to those that would speak to him of it, set quite a few eyes watching for him with promise of reward should they return her 'wayward servant' to her.

Additionally she blocked him even from making money at gambling by forbidding her patrons to play him at cards or any other form of monetary risk. Considering the gravely low wages she afforded him for his chores Jack did not see himself ever obtaining the necessary funds to properly bribe his way out of the brothel.

Force certainly wasn't an option, either; Jack had never really been the best fighter, and he had a feeling he would be grossly outnumbered immediately upon his exit of the house. He mulled over the idea of assassination constantly, but Jack knew he would be the first and probably only suspect in such a murder as soon as Mrs. Mapleton was discovered dead.

He could try framing another girl for the act, but that wouldn't remove him as a suspect, and people were well aware of his prowess in manipulation; the incident would be investigated thoroughly, and the slightest slipup would mean the end of him.

Besides, he thought with a sigh, framing people for murder really wasn't his cup of tea, and despite how hard he might occasionally tell himself he was, he knew all of the girls here now; having their death on his conscience might bother him a little.

For the next week Jack drowned his sorrows in extremely cheap alcohol and the sweet embrace of Anne's arms, at least when she allowed him to hold her and didn't insist on tying him up. For it had become painfully clear to Jack that his options weren't really options at all; he simply had a list of unpleasant choices to choose from.

Despite how much distaste he had for continuing on as the errand-boy for the devil's own Mrs. Mapleton, he had to swallow whatever still remained of his pride and bite this ignoble bullet. Brainstorm as he might, when the thunderheads of his thoughts had cleared, he was still just as damnably stuck waiting for something to happen that might change the nature of his situation.

So it was that a full month passed by, and despite his inordinate amount of ass-kissing, the Madam was not only unimpressed, but she seemed to always think he wasn't suffering enough. She routinely gave him the most vile, degrading tasks she could think of and he would swear that she was perhaps dissatisfied that he did them so readily.

Jack suspected that she would have liked him to groan and moan concerning her orders to clean the latrine, and as he watched her reactions further it became clear to him that she actually just wanted him unhappy.

Accordingly, Jack spent all of his time thereafter moping about and wearing his feelings about where he now stood on the outside. Sure enough, Mrs. Mapleton was amused in short order. Jack sighed when he observed her up on the balcony tittering happily with the girls as she watched him mopping the floor in a dejected fashion.

Unfortunately, knowing what Mrs. Mapleton wanted did him no good; how do you barter with someone who just wants to see you miserable? Jack thought on it for a while and decided he had only one real option, and it was certainly a stretch; he would have to act as depressed as possible until the old bag finally got tired of him to the point of forgiving him their earlier rivalry.

Jack didn't much care for an action like this one, of course; he wasn't actually a gambling man, when he played cards he usually cheated. Doing something that wasn't a sure thing went against his nature, but for lack of any better ideas or promise of any to come, Jack resigned himself to the abysmal notion of 'hope'.

Jack raised a dirty glass of cheap swill in toast to his own inner thoughts, "Here's to finding out just how unlucky I am."

The answer came to Jack a few days later; a large brute of a man walked up to him and, quite unexpectedly, grabbed a firm hold of Jack's crotch. Jack squeaked a little, such was his surprise, and he requested an explanation in a voice a timber higher than usual, "Sir, you seem to have misplaced your hand."

The huge bald fellow only smiled, and Jack realized at once that the man was missing many of his teeth and that the odor of his breath was most foul. Jack recoiled as much as the firm grip on his genitals allowed, trying a different approach, "I see… well, sorry to inform you of this my good man but I'm just a waiter here; I'm not up for sale and I certainly prefer the fairer sex."

"Belay that." Mrs. Mapleton approached from across the way, "As I informed this man only moments ago, you are indeed a member of this brothel, and if he's willing to pay for a bite of the forbidden fruit, I am loathe to turn him down."

Jack squirmed, gently taking the other man's hand and guiding it away from his gender; thankfully, his grip released and Jack could breathe again. "Would you be so kind as to allow me a word with the Madam concerning our contract?"

The brutish man frowned but didn't move to interject when Jack receded to talk closely to Mrs. Mapleton, whispering, "I'm sorry if I failed to inform, mistress, but I have only ever been in the company of women and would made an exceedingly poor whore."

Mrs. Mapleton smiled, sharing his conspiratorial lowered voice, "That's quite all right, my dear; I'm sure with a little practice you will get the hang of it. After all, you have very fair features; the kind of softness often lusted after by men like these."

Jack's eyebrow twitched and he steepled his hands together, touching his index fingers to his lips before continuing, "All right, I get it; you still want me to pay further for past damages. I understand, and I will happily continue to make it up to you in other ways, but not like this, you must understand; I simply have no interest in men."

The mirth left the Madam's face and her voice was low and menacing, "I couldn't give two shits what you want, and you aren't the one who decides how pay for your hubris, I am. You're going to go with this man and suck his prick or allow him to shove himself into your ass and you're going to do it because I told you to."

Jack hated where this was going, knew where this was going, but found himself having to play it out anyways, "And if I should refuse?"

Mrs. Mapleton's smile returned, only it was cruel and without mirth, "Then you will find yourself thrown out of my house, out there on the streets where we both know you won't live to see morning."

Jack ran a hand through his hair, pacing a little before returning to continue the fierce whispered conversation, "You don't know that; I might just make it off of this fucking island; what's more do you really want to risk losing the chance to continue torturing me daily over this?"

The mistress shook her head, still smiling, "I know you have been snooping, and in case your busy bees didn't tell you, I have warned Vane's men that you might try to bolt today; you haven't a snowballs chance in hell of survival. Besides, we both know you're a coward."

Jack took offense but decided that showing it would only please the matron further. So instead he chose the path of least resistance, since she was right; he couldn't defy her now, not like this. "Very well, I shall see this… gentleman to my room immediately."

Mrs. Mapleton looked surprised and Jack realized she has expected him to whine or complain quite a bit more. It gave him some satisfaction to know that she had just realized he wasn't as predictable as she had apparently foreseen.

He would be sure to continue to surprise her in the immediate future, because he'd be damned if he was going to literally be taking this lying down. She only waved in obviously feigned indifference, "Go on, then, make me some money, whore."

Jack approached the hairy man off to the side and smiled, "Would you mind if we went somewhere more private to have a chat?"

The burly man smiled in an overt display of sexual avarice, and he clamped a hand on Jack's ass as they strode around the corner and into the small hallway that led to Jack's room at the far end (he of course had the worst accommodations possible thanks to Mrs. Mapleton, only one step up from a broom closet).

The Madam, for her part, smiled as she watched the two of them round the corner, and seeming to be satisfied with what she saw, she moved on to attend to other business. Jack glanced over his shoulder and waited until they were down the hall a ways before talking to the beefy sailor in hushed tones, "There has been a reason that I haven't been sleeping with anyone despite my occupancy in a house of pleasure…"

The boorish man looked confused, "…What?"

Jack started over, speaking slowly, "I haven't been fucking the women here, or any men for that matter…" he gave the man a conspiratorial look before leaning in to whisper very softly, "I've got the cock rot."

The other man made a face of disgust and backed away a few paces. Jack went on, "The Madam only now found out, and I'm sure you can understand why I don't want to go public with such shaming news; I will likely be dead by this time next month and my name is all I have left, tarnished as it already is…"

The sailor only nodded, his face still twisted into a look of distaste. Jack smiled, "The Madam may continue to solicit me as a genuine whore to gentlemen of your… tastes, but only because she is so kind-natured and doesn't want everyone knowing about my condition. If I could ask you a favor, could you kindly tell those you know who might be interested in me the truth so as to avoid further confusion?"

The man nodded, and then walked away quickly, as if merely standing next to Jack might cause his member to shrivel up. Jack smiled; heading into his room to open the musty bottle that contained what was left of the disgusting watered-down liquor he had stored there. He toasted himself, "Another satisfied customer, Jack."

A number of weeks passed, and the discussion Jack knew was coming finally arrived; the Madam asked him to accompany her to her small office upstairs. Jack had expected this talk was due, but he had to admit he was surprised with the secrecy; Mrs. Mapleton never used her office.

Jack realized as they entered that the use of the small room might have been partly to veil a surprise for Jack; the burly fellow he had lied to weeks ago stood within, his arms crossed over his chest and staring at Jack in a manner most surly.

Jack had learned after that day that the man's name was Pits, or at least that was what the other members of his crew called him, for no right-thinking father would ever name his child Pits. Jack gave him a friendly smile, "Hello there, old friend."

Mrs. Mapleton raised an eyebrow and shut the door behind them. She folded her hands neatly in front of herself and addressed Mr. Pits, "Sir, I have brought my whore here to clarify the awful rumors he has spread due to a capricious nature left unchecked."

Jack fidgeted but didn't say anything as Pits continued to glare at him. Finally the bear of a man spoke, "You lied to me?"

Jack cleared his throat, weighing his options as Mrs. Mapleton needled him with her own intense gaze from the side. He had been found out as he had known he would, but he hadn't expected the Madam to involve the man that he had initially lied to.

He had planned on lying further to set the old hag awry for at least a while longer, but clearly she was not only unwilling to allow him the opportunity, she intended to bring things to a head immediately with the bitter irony of the whole 'dishonest whore' bit.

At last he licked his dry lips and spoke, "I admit it was a story in poor taste, by my matron here simply will not accept that I am uninterested in men; I am in the awkward position of trying to make her happy while maintaining the chastity of my asshole… surely you can understand I meant no real harm?"

His fast-talking seemed to have had effect by the look of confusion on Mr. Pits' face, but Mrs. Mapleton stepped in the rain on his parade as she was prone to do, "In other words, this whore fails to understand that the Madam of the house calls the shots, and that he should spread his legs and do what he is told…"

Jack couldn't help but ruffle indignantly a bit at that last part, and Mrs. Mapleton smiled, ever enjoying his discomfort, "…he will be punished and then offered to you free of charge as apology for the obvious lack of discipline."

Jack's eyebrows shot up, "Punished? Whatever did you have in mi…? Oh." Jack swallowed as Mrs. Mapleton opened a cabinet on the other side of the room which contained a large assortment of paddles, switches, straps and even a few cat-o-nine-tails.

These were obviously devices held for the use of more eccentric guests to the whore-house, but clearly Mrs. Mapleton was not averse to putting them to other uses. She reached up, plucking a thick leather strap from a nail on the closet door.

She turned, taking a few steps forward and smiling when Jack took a few steps back, "Mr. Pits, if you could kindly block the door; I doubt he is stupid enough to run from me, but I'd do him the favor of removing the possibility."

The huge bald man smiled and moved to the indicated location, folding his arms over his chest again, presenting a very intimidating and immovable-looking blockade.

Jack felt cornered, and the implications of what she planned careened through his mind; he was already seen in a poor light by those that resided on the island, if word of his predicament with Mrs. Mapleton got out, any chance of him sailing under the black would be forever ruined.

"Madam, you aren't thinking this through; if you persist in your current line of action, it is going to have to become irrevocably clear to Mr. Pits that I am not never ever was a whore employed by you." Jack moved to put the small desk at the back of the room between him and the elderly woman as she advanced.

Mrs. Mapleton chuckled, "Quite the opposite; I intend to make it painfully clear to you that you are mine, as you are the only deluded person in this house who fails to understand his place."

Jack lost his composure as she circled the desk, chasing him in a circle to avoid her, "You are mad if you think I will allow you to treat me like this; you force a lion into a corner, Mrs. Mapleton. Be aware that anything that happens from here is on you!"

She scoffed again, not relenting in her pursuit as she replied, "You strike me and you die here, boy; in fact, if you don't start being compliant very soon I will have you thrown onto the street just to enjoy watching how far down the street you can make it from my balcony."

Jack hadn't wanted to play his ace yet, but he was out of options, "Anne would never throw me out!"

Mrs. Mapleton smiled, "Perhaps, but look me in the eyes and tell me that she won't stand aside while I have Mr. Pits here toss you to the dogs."

Jack froze, unable to contradict her fully; he'd love to say that Anne would step in to defend him, but Mrs. Mapleton had been paying her handsomely for a while now, and Jack had always known his fondness of her wasn't necessarily reciprocated.

Mr. Pits apparently decided that their ridiculous dance around the desk was fated to end then, for he took Jack's moment of indecision to lunge forward and grab him, slamming him down into the table, "Stop talking back to the Madam, whore, and do what you're told. My cock's gone soft for all this waiting and I intend to be in you soon."

Jack's eyes were wide as he contemplated the multiple threats of both Mr. Pits' promise as well as Mrs. Mapleton's, helpless to stop her from reaching him now that he was firmly secured to the desk by Mr. Pits' bulging arms.

To his dismay, Mrs. Mapleton pulled his pants down to his ankles, leaving the stark white nakedness of his buttocks plain to see. She leaned in before getting started, though, "Are we clear on where we stand yet, Jack?"

Jack didn't answer, once again rendered speechless by yet another situation that offered no real options except ugly endings and uncomfortable ends (this time quite literally).

Mrs. Mapleton seemed to take his quiet for subjugation and put a hand on Mr. Pits' arm, "Why don't you stand by the door again, honey; I think our whore is finally starting to get it."

Pits grunted and did as asked; seeming bored with the interaction and impatient to begin the parts of the encounter that Jack was dreading the most. Nonetheless he waited as patiently as one of his temperament could, staring at Jack's back-side in a manner that left Jack decidedly uncomfortable.

Jack remained on the desk, knowing that running wouldn't help him and finally admitting to himself that he was scared; terrified, actually, of what Mrs. Mapleton would do to him should he continue to resist the awful things she had planned for him.

She was apparently more cruel and sadistic than he had predicted before, and though he couldn't immediately imagine how the situation he was in could get worse, he suddenly found himself without doubt that she could.

The Madam held herself in a manner that suggested she knew he had gone spineless, and her tone spoke that she had in fact been anticipating this exact moment of epiphany, "Poor, poor Jack, thought he was so god-damned clever. Thought that if he waited me out, I'd slip up, and he'd get another go at me."

The strap flashed down unexpectedly, and Jack gripped the sides of the desk, crying out in pain. Mrs. Mapleton went on, "A whore house is a training ground for dealing with conniving fucks like you, Jack, and I certainly didn't become Madam of this establishment by being lucky."

Another swat and Jack writhed on the desk, gritting his teeth and moaning at the extreme discomfort those wicked red welts on his posterior now caused. Worse, Pits was licking his lips in an unsavory way as Jack wiggled about, making the former sailor even more stressed.

Mrs. Mapleton seemed yet to be finished both with his punishment or her lecture, as her voice droned on, "You are a whore now, Jack; because it's the lowest thing I can feasibly make you into and still curry a profit. But…"

Another stinging swat and Jack called out loudly, unable to check his voice against the searing pain that erupted from being struck in the same tender area twice. He was all too aware that loud yells would undoubtedly be heard from the main lobby outside of the office.

He knew that there would have been those that took notice of him entering the room with Mrs. Mapleton, and even if not, he would certainly be seen exiting after such a loud spectacle. Even the dumbest of Nassau's pub-crawlers would likely deduce what had happened to him.

The thought of what was going to happen to the shambles of his once-great reputation stung almost as much as the next swat Mrs. Mapleton delivered, which to his great shame caused him to cry out in a high-pitched and perhaps even lady-like fashion.

Unable to bear another seething attack Jack finally retreated from the desk, his hands going to his bottom as he begged mercy, "Please, I…"

Surprise registered again on his face as Mr. Pits hefted him up from behind and placed him back on the desk, "Don't be such a bitch about it; take your beating as if you were actually a man."

Stunned by the vulgar but well-timed insult by Mr. Pits, Jack didn't move as Mrs. Mapleton swatted him again, "He can't help himself; he has always been weak. We'll give him a few more to remember that by, and I'm sure he won't soon forget himself again."

Jack wriggled under the muscular man's grip but Mr. Pits was far stronger; a not-so-promising glimpse of what was to come once this preliminary torture finally ceased. Mrs. Mapleton, for her part, gave him the promised few swings of remembrance and then leaned in to smile at him as he panted on the desk, "I told you that you would regret it."

She hung the strap back on its nail on the closet door and then shut it, still smiling. Giving him one last pointed look, she turned and simply walked out then, pulling the door shut behind her. As the door closed, Jack became uniquely aware of Pits' hot, heavy breath behind him.

His pants were still down, and from the expression on the sailor's face, the entire painful episode had actually excited the man. This did not bode well for Jack, of course, and with diplomacy now out of the window thanks to Mrs. Mapleton's maneuvering, his options were now looking long, hard and painful as Pits pulled his own pants down.

Stalling for time because that was the only thing left to him even if it only prolonged his agony, Jack gave him a weak smile, "May I at least remove myself from the desk?"

Pits shook his head, smiling, "I kind of like it like this, and you are all trussed up here ready and all, no reason not to get right to business."

Jack grimaced, finally allowing the despair he had been fighting for so long to take a firm grip of him; he couldn't lie to himself anymore. He had been, was, and for the foreseeable future would always be… screwed.


End file.
